1-(3-Dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride → HCID 88403696, compound

Participants

Reaction Steps

To a solution of the title A compound from Example 3 (2.2 g, 12.5 mmol) and (trans)-4-amino-3,4-dihydro-2,2-dimethyl-2H-pyrano[3,2-c]pyridin-3-ol (1.1 g, 5.7 mmol) (prepared according to EP 0 205 292 A2) in dimethylformamide (5 ml) under argon, 1-(3-dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride (2.2 g, 10.8 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 2 hours and then partitioned between water (pH ~11) and ethyl acetate. The organic phase was separated and the aqueous phase was reextracted with ethyl acetate and the combined organic phase was washed with water, aqueous sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated and the residue was purified by flash chromatography on silica gel (acetone:dichloromethane/1:4) to yield a colorless solid (470 mg) which was crystallized from acetonitrile to provide the title compound, m.p. 233°-236° C.

Provenance & Evidence